Ultrasound-assisted, low-solvent and acid/base-free synthesis of 5-substituted 1,3,4-oxadiazole-2-thiols as potent antimicrobial and antioxidant agents

Yarmohammadi, Elahe; Beyzaei, Hamid; Aryan, Reza; Moradi, Ashraf

doi:10.1007/s11030-020-10125-y

Cited by 17 publications

(7 citation statements)

References 58 publications

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“…Compound 35 (5-(4-fluorophenyl)-1,3,4-oxadiazole-2-thiol) (Figure 13) had the greatest potential, as it showed stronger activity against E.coli and S. pneumoniae compared to ampicillin, and it was active against P. aeruginosa-over 100 times stronger. Additionally, it had antifungal activity against A. fumigatus better than terbinafine [69].…”

Section: Antibacterial Activity Of Amino Derivatives Of 134-oxadiazolementioning

confidence: 99%

Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

Glomb

Świątek

2021

IJMS

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The worldwide development of antimicrobial resistance forces scientists to search for new compounds to which microbes would be sensitive. Many new structures contain the 1,3,4-oxadiazole ring, which have shown various antimicrobial activity, e.g., antibacterial, antitubercular, antifungal, antiprotozoal and antiviral. In many publications, the activity of new compounds exceeds the activity of already known antibiotics and other antimicrobial agents, so their potential as new drugs is very promising. The review of active antimicrobial 1,3,4-oxadiazole derivatives is based on the literature from 2015 to 2021.

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Section: Antibacterial Activity Of Amino Derivatives Of 134-oxadiazolementioning

confidence: 99%

Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

Glomb

Świątek

2021

IJMS

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“…[58] Compounds that have the ability to reduce oxidative stress can, therefore, find application in medicine. [59,60] As discussed above, both indoles [25][26][27][28] and 1,3,4-oxadiazoles [4][5][6][7][8] are known as antioxidants, and 2-(indol-2-yl)-1,3,4-oxadiazoles were also reported to possess antioxidant properties. [61] Moreover, compound 16 emerged in a recent high-throughput screening whose purpose was to find potential treatments to a rare hereditary mitochondrial disease, Friedreich's ataxia (FA) (Voller et al, unpublished).…”

Section: Biologymentioning

confidence: 99%

“…Oxadiazoles, which exist in four isomeric forms, are used in drug discovery research for a variety of reasons: They can serve as a part of the pharmacophore, as flat aromatic linkers, or as moieties modulating molecular properties. [1] In recent years, interest in 1,3,4-oxadiazoles has especially risen [2] as apparent from their wide use in development of antiparasitic, [3] antioxidant, [4][5][6][7][8] anticonvulsant, [9] antimicrobial, [4] anticancer, [10][11][12] anti-HIV, [10] anti-inflammatory, [13] analgesic, [14] and antitubercular agents [15] as well as α-glucosidase inhibitors. [16,17] Moreover, 1,3,4-oxadiazole heterocycles are good bioisosteres of esters and amides, which can substantially contribute to hydrogen-bonding interactions with receptors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 5‐[(1H‐indol‐3‐yl)methyl]‐1,3,4‐oxadiazole‐2(3H)‐thiones and their protective activity against oxidative stress

Iškauskienė

Kadlecová

Voller

et al. 2021

Archiv der Pharmazie

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A small library of 2-[(1H-indol-3-yl)methyl]-5-(alkylthio)-1,3,4-oxadiazoles was prepared, starting from indole-3-acetic acid methyl ester and its 5-methyl-substituted derivative. The synthetic route involved the formation of intermediate hydrazides, their condensation with carbon disulfide, and intramolecular cyclization to corresponding 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones. The latter were then S-alkylated, and in case of ester derivatives, they were further hydrolyzed into corresponding carboxylic acids. All 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones and their S-alkylated derivatives were then screened for their protective effects in vitro and in vivo. Methyl substitution on the indole ring and propyl, butyl, or benzyl substitution on sulfhydryl group-possessing compounds were revealed to protect Friedreich's ataxia fibroblasts against the effects of glutathione depletion induced by the γ-glutamylcysteine synthetase inhibitor, buthionine sulfoximine. Two of the active compounds also reproducibly increased the survival of Caenorhabditis elegans exposed to juglone-induced oxidative stress.

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“…Numerous reports have highlighted their chemistry and uses. Diverse biological activities, such as antimycobacterial, antioxidant, antimicrobial, anti-infammatory, analgesic, antipyretic, anticonvulsant, and antidiabetic, have been associated with the 1,3,4-oxadiazole derivatives [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Antidiabetic Activity of Oxadiazole Derivative in Rats

Qazi

Ahmad

Sahibzada³

et al. 2023

Evidence-Based Complementary and Alternative Medicine

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The oxadiazole ring has long been used for the treatment of several diseases. This study aimed to analyze the antihyperglycemic and antioxidant roles of the 1,3,4-oxadiazole derivative with its toxicity. Diabetes was induced through intraperitoneal administration of alloxan monohydrate at 150 mg/kg in rats. Glimepiride and acarbose were used as standards. Rats were divided into groups of normal control, disease control, standard, and diabetic rats (treated with 5, 10, and 15 mg/kg of 1,3,4-oxadiazole derivative). After 14 days of oral administration of 1,3,4-oxadiazole derivatives (5, 10, and 15 mg/kg) to the diabetic group, the blood glucose level, body weight, glycated hemoglobin (HbA1c), insulin level, antioxidant effect, and histopathology of the pancreas were performed. The toxicity was measured by estimating liver enzyme, renal function, lipid profile, antioxidative effect, and liver and kidney histopathological study. The blood glucose and body weight were measured before and after treatment. Alloxan significantly increased blood glucose levels, HbA1c, alanine transaminase, aspartate aminotransferase, urea, cholesterol, triglycerides, and creatinine. In contrast, body weight, insulin level, and antioxidant factors were reduced compared to the normal control group. Treatment with oxadiazole derivatives showed a significant reduction in blood glucose levels, HbA1c, alanine transaminase, aspartate aminotransferase, urea, cholesterol, triglycerides, and creatinine as compared to the disease control group. The 1,3,4-oxadiazole derivative significantly improved body weight, insulin level, and antioxidant factors compared to the disease control group. In conclusion, the oxadiazole derivative showed potential antidiabetic activity and indicated its potential as a therapeutic.

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Ultrasound-assisted, low-solvent and acid/base-free synthesis of 5-substituted 1,3,4-oxadiazole-2-thiols as potent antimicrobial and antioxidant agents

Cited by 17 publications

References 58 publications

Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

Synthesis of 5‐[(1H‐indol‐3‐yl)methyl]‐1,3,4‐oxadiazole‐2(3H)‐thiones and their protective activity against oxidative stress

Evaluation of Antidiabetic Activity of Oxadiazole Derivative in Rats

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